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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014527
Secondary Accession Numbers
  • HMDB14527
Metabolite Identification
Common NameOxyphencyclimine
DescriptionOxyphencyclimine is only found in individuals that have used or taken this drug. It is an anticholinergic drug (trade name Daricon) used in treating peptic ulcers.Oxyphencyclimine binds the muscarinic acetylcholine receptor. It may block all three types of muscarinic receptors including M-1 receptors in the CNS and ganglia, M-2 receptors in the heart (vagus) and M-3 receptors at the parasympathetic NEJ system. The muscarinic acetylcholine receptors mediate various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Oxphencyclimine inhibits vagally mediated reflexes by antagonizing the action of acetylcholine. This in turn reduces the secretion of gastric acids in the stomach.
Structure
Data?1582753189
Synonyms
ValueSource
OxiphencycliminumHMDB
Oxyphencyclimine hydrochlorideHMDB
Oxyphencyclimine, (+-)-isomerHMDB
Oxyphencyclimine monohydrochlorideHMDB
Chemical FormulaC20H28N2O3
Average Molecular Weight344.4479
Monoisotopic Molecular Weight344.209992772
IUPAC Name(1-methyl-1,4,5,6-tetrahydropyrimidin-2-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
Traditional Nameoxyphencyclimine
CAS Registry Number125-53-1
SMILES
CN1CCCN=C1COC(=O)C(O)(C1CCCCC1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C20H28N2O3/c1-22-14-8-13-21-18(22)15-25-19(23)20(24,16-9-4-2-5-10-16)17-11-6-3-7-12-17/h2,4-5,9-10,17,24H,3,6-8,11-15H2,1H3
InChI KeyDUDKAZCAISNGQN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydropyrimidines. Hydropyrimidines are compounds containing a hydrogenated pyrimidine ring (i.E. Containing less than the maximum number of double bonds.).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentHydropyrimidines
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Hydropyrimidine
  • 1,4,5,6-tetrahydropyrimidine
  • Benzenoid
  • Imidolactam
  • Tertiary alcohol
  • Carboxylic acid ester
  • Azacycle
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Aromatic alcohol
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.057 g/LNot Available
LogP3.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available183.878http://allccs.zhulab.cn/database/detail?ID=AllCCS00000930
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.057 g/LALOGPS
logP2.89ALOGPS
logP2.62ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)11.53ChemAxon
pKa (Strongest Basic)8.37ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area62.13 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.13 m³·mol⁻¹ChemAxon
Polarizability38.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+181.62931661259
DarkChem[M-H]-178.40431661259
DeepCCS[M+H]+181.21430932474
DeepCCS[M-H]-178.85630932474
DeepCCS[M-2H]-212.10630932474
DeepCCS[M+Na]+187.33330932474
AllCCS[M+H]+183.332859911
AllCCS[M+H-H2O]+180.332859911
AllCCS[M+NH4]+186.132859911
AllCCS[M+Na]+186.932859911
AllCCS[M-H]-186.432859911
AllCCS[M+Na-2H]-186.732859911
AllCCS[M+HCOO]-187.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OxyphencyclimineCN1CCCN=C1COC(=O)C(O)(C1CCCCC1)C1=CC=CC=C13223.4Standard polar33892256
OxyphencyclimineCN1CCCN=C1COC(=O)C(O)(C1CCCCC1)C1=CC=CC=C12461.9Standard non polar33892256
OxyphencyclimineCN1CCCN=C1COC(=O)C(O)(C1CCCCC1)C1=CC=CC=C12636.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxyphencyclimine,1TMS,isomer #1CN1CCCN=C1COC(=O)C(O[Si](C)(C)C)(C1=CC=CC=C1)C1CCCCC12691.6Semi standard non polar33892256
Oxyphencyclimine,1TBDMS,isomer #1CN1CCCN=C1COC(=O)C(O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1CCCCC12892.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxyphencyclimine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0900000000-62b94f60aad1cc5695ee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxyphencyclimine GC-MS (1 TMS) - 70eV, Positivesplash10-03di-1190000000-5a19ecbe24d87eaa2a2b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxyphencyclimine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxyphencyclimine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 10V, Positive-QTOFsplash10-0002-2539000000-9f10009b6785f6b09c622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 20V, Positive-QTOFsplash10-03yj-9634000000-28e858c9837c80aa0f762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 40V, Positive-QTOFsplash10-0a5c-9200000000-0e1682e1ccaed79956852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 10V, Negative-QTOFsplash10-052f-0937000000-10e2c4c647735b402eae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 20V, Negative-QTOFsplash10-004l-9544000000-f3a900d92d20c254c7262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 40V, Negative-QTOFsplash10-004i-9500000000-e68167172a319a617c3d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 10V, Negative-QTOFsplash10-000f-0908000000-4c1776351673c879c0482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 20V, Negative-QTOFsplash10-000i-0912000000-6de8c9ff18a495633e732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 40V, Negative-QTOFsplash10-0079-0910000000-541fbf8ab350d434ae882021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 10V, Positive-QTOFsplash10-0002-0009000000-934dd5cc037389487cbd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 20V, Positive-QTOFsplash10-0002-2938000000-509796f4416f067f23c82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxyphencyclimine 40V, Positive-QTOFsplash10-001j-9310000000-366f1fc7f3dcd6c0f6752021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00383 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00383 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00383
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4481
KEGG Compound IDC07851
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxyphencyclimine
METLIN IDNot Available
PubChem Compound4642
PDB IDNot Available
ChEBI ID518489
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular weight:
66127.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [PubMed:1426023 ]
  4. Schjelderup L, Kozlowski MR, Weissman A, Aasen AJ: Antimuscarinic effects of (R)- and (S)- oxyphencyclimine hydrochloride. Pharm Res. 1988 Apr;5(4):236-7. [PubMed:3247303 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [PubMed:1426023 ]
  4. Schjelderup L, Kozlowski MR, Weissman A, Aasen AJ: Antimuscarinic effects of (R)- and (S)- oxyphencyclimine hydrochloride. Pharm Res. 1988 Apr;5(4):236-7. [PubMed:3247303 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [PubMed:1426023 ]
  4. Schjelderup L, Kozlowski MR, Weissman A, Aasen AJ: Antimuscarinic effects of (R)- and (S)- oxyphencyclimine hydrochloride. Pharm Res. 1988 Apr;5(4):236-7. [PubMed:3247303 ]